Reaktion #535366

Reaktionsgleichung

ferulic acid

triethylamine

3-hydroxytyramine

→

N-trans-feruloyldopamine

Lösungsmittel

dichloromethane

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe dichloromethane is evaporated off under vacuum
2. 2
   workup.ADDITION30 mL of water are added to the remaining solution
3. 3
   Sonstigethe mixture obtained
4. 4
   Extraktionis extracted with ethyl acetate (3×75 mL)
5. 5
   WaschenThe organic phase is successively washed with 100 mL of 1N HCl solution, 100 mL of water and 100 mL of 1M sodium bicarbonate (NaHCO3) solution
6. 6
   TrocknenIt is then dried over sodium sulfate
7. 7
   Sonstigeevaporated to dryness
8. 8
   SonstigeThe product obtained

Vorschrift

A solution of ferulic acid (300 mg; 1.54 mmol) and of triethylamine (1.5 eq; 2.31 mmol) in DMF (3.5 mL) is cooled to 3 or 4° C. using an ice bath. An amine, 3-hydroxytyramine (dopamine) (1 eq; 1.54 mmol) is added to the medium, followed by addition of a solution of BOP (benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; (1 eq; 1.54 mmol) in dichloromethane (3.5 mL); the mixture is stirred for about thirty minutes in the ice bath and then for 20 hours at room temperature. Stirring is then stopped and the dichloromethane is evaporated off under vacuum. 30 mL of water are added to the remaining solution and the mixture obtained is extracted with ethyl acetate (3×75 mL). The organic phase is successively washed with 100 mL of 1N HCl solution, 100 mL of water and 100 mL of 1M sodium bicarbonate (NaHCO3) solution. It is then dried over sodium sulfate and evaporated to dryness. The product obtained is in the form of a white precipitate after chromatography on a column of silica gel.

Quelle